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The following is a timeline of Prison Break and briefly describes what happened and when. Season 5 retcons the events, placing Michael's fake death in 2010 instead of 2005.
- Frank Tancredi was born.
- Charles Westmoreland was born.
- Christina Scofield is born.
- Brad Bellick was born.
- Theodore Bagwell's fourth grade: T-Bag sent to a juvenile hall for setting fire in his teacher's home.
- Paul Kellerman was born.
- March 17: Lincoln Burrows was born
- D. B. Cooper hi-jacked a plane and parachuted out with $5 million in cash.
- James Whistler is born.
- May 1 : Sara Scofield is born.
- Kristine Pace was born.
- The Miami-Dade Penitentiary Women's Facility is built.
- Christina Scofield Fakes her own death to work for The Company.
- Henry Pope began his life as a warden.
- Kristine Pace and Paul Kellerman parted and never see each other again.
- McGrady was born.
1996 - 1997
- Between Sept 8, 1996 and Sept 8, 1997: Lincoln borrowed $90,000 to pay for Michael's university education.
- Cameron Mahone is born.
- "Brother's Keeper" takes place.
- A few months before 9/11: Caroline Reynolds talked to Terrence Steadman.
- Terrence Steadman is "killed" by Lincoln Burrows
- Haywire was sentenced and sent to Fox River.
- Sucre meet Maricruz
- "Brother's Keeper" takes place.
- Abruzzi was sentenced and sent to Fox River.
- Sucre and Maricruz began dating.
- Bellick becomes the head of COs.
- McGrady was sent to Sona.
- July: Sucre was sentenced and sent to Fox River.
- December: Michael buys a boat and names it Christina Rose.
- Michael starts planning his escape from Fox River.
- January: Michael started visiting the tattoo parlor.
- February: C-Note was sentenced and sent to Fox River.
- March 8: Michael married Nika Volek.
- March 9: Michael robbed the bank.
- April 11: Michael was sent into Fox River.
- May 11: Original date of Lincoln's execution. "By the Skin and the Teeth" take place.
- Somewhere between May 25 and May 31: The break out. "Go" and "Flight" take place.
- May 26: Lincoln's revised execution date.
- June 1: "Buried" and "Dead Fall" take place; Frank Tancredi dies.
- June 2: "Unearthed" take place.
- June 3: "Rendezvous" take place.
- June 4: "Bolshoi Booze" and "Disconnect" take place. Reynolds visits Denver, Colorado.
- Probably June 5: "The Killing Box" take place.
- June 6: "Sweet Caroline" take place.
- June 9: Old Mexican Man's wife died.
- June 16: "Panama" and "Fin Del Camino take place.
- June 17: "Sona" and "Orientación" take place.
- June 18: "Orientación" take place.
- June 19: "Fire/Water" take place.
- June 20: "Call Waiting" and "Good Fences" take place.
- November 4: The Miami-Dade breakout takes place. Michael fakes his death. ("Prison Break: The Final Break", original timeline, prior to retcon)
- June 13: Date of Mahone going to the juries.
- Four years after 2005: General Krantz is executed. Danny Hale's widow, Allison, visits Congressman Kellerman. Sara, Lincoln, Mahone and Sucre visit Michael's grave.
- November 4: The Miami-Dade breakout takes place. Michael fakes his death. ("Ogygia", retconned timeline)
- The trailer for Season 3 says that the convicts are on the run for one year, simplified for viewers who haven't seen the show in a year's time (TV land time). In fact Season 2 in its entirety takes place within only a month.
- Caroline Reynolds is a presidential candidate in Season 1, however the United States presidential election was, in the real world, scheduled to take place in November 2004, 6 months before she was sworn into office after her predecessor's assassination by the Company in "Flight ." In the same episode, Reynolds is mentioned as being the 46th President of the United States; from this can be surmised that, in the Prison Break universe, some Presidents did not serve a second term as they did in reality, where the 43rd President was serving a second term in 2005. In "Sweet Caroline," Reynolds runs again, in June 2005.
- Originally, in Prison Break: The Final Break, Michael Scofield fakes his death in 2005. Season 5 alters the timeline so that Michael instead fakes his death in 2010.